Process for the production of amino acids



acids of the type of glycocoll, alanine, etc. maybe The total yield of44 to 45 lbs. is equal to 10 4,0 Se precipitate 01 ammonium Chloridewith acid which comprises ammonolysis of chloracetic o Patented June 27,"1939 I i I I 2,163,594

UNITED STATES PATENT OFFICE I I 2,163,594

rnocns's FOR THE PRODUOTiONOF AMINO ACIDS William H. Engels, Rahway, andGustav A. Stein,

Elizabeth, N. J.,' assignors to Merck & C0.Inc., Rahway, N. J., acorporation of New Jersey 7 No Drawing. Application December 1, 1936,

, Serial No. 113,608

4 Claims. (Cl. 260-534) 7 This invention relates to a valuableimprovewith a small amount of 80% alcohol, then with ment in themanufacture of amino carboxylic 99% alcohol, and dried. 'The'yield ofpure aminoaclds by ammonolysis of appropriately selected acetic acidthus obtained is 42 lbs. The product halogenated organic acids, in thepresence of ,an has a melting point of about 226 C., and is free 5ammonium halide. from ammonia when tested with N esslers reagent. 5

In the old art, these amino carboxylic acids B'y evaporating the motherliquors to dryness have been produced by reacting upon halogenated andtreating with, a small amount of water, 3 to 4 organic acids witha'large excess of ammonia. lbs. more of pure aminoacetic acid can be 0b-We have now found that such amino carboxylic tained.

obtained in much higher yield than heretofore; 59-60% of theory.

and that the excess of ammonia required in the From the foregoingdetailed example, it will be old process may be greatly reduced, if theamevident to those skilled in the art that the reac-- monolysis of theappropriatelyselected halogenattion therein described may be adapted,also, to

ed organic acids is carried out in the presence of the production ofother similar amino carboxyli'c l5 1 an ammonium halide, such asammonium chloacids by appropriate selection of the halogenated ride,organic acid and suitable adjustment of the other In order to illustrateour new process'in detail, working conditions. Thus, it will be readilyunthe following specific example is given: derstood, that ifchlor-propionicacid is substi- Exambze tuted for the chloracetic acidexemplified, and the so other factors of the reaction and purificationAbout 320 lbs. of ammonium chloride are, susprocesses properly adjusted,pure alanine will be pended in about 110, liters of water and heated toobtained in substantial quantity.

about 5 C. A s t p a u about 225 Therefore, the present 'nvention is notto be lbs. of concentrated ammonia and a solution of limited to thespecific detailed illustration given, 2 about 94.5 lbs. of chlor aceticacid in 100 lbs; of but may be modified, as indicated, without dewaterare added simultaneously, under s irri g, parting'from its spirit andscope. at such a rate that about 15 to' minutes are re- We laim as ourinvention:

quired- The mixture is stirred and maintained at 1. A process for'theproduction of amino car 30 95. for about 1% hours. The mixture is cooledboxylic acids which comprises ammonolysis of an 30 and the ammoniumchloride removed by filtraappropriately selected'halogenated organicacid tion. The filtrate is concentrated in vacuo to n th presence of n amoni m halide, the

- about 65 liters. A te o a u said halide being retained inthe reactionmixture ride is again filtered off, and aminoacetic acid is throughoutth e ti reaction,

' p e p by adding about 2'70 liters f m t yl 2. A process for theproduction of amino caralcohol under Stir ing. A t a d g abflut boxylicacids which comprises ammonolysls of an 8 hours. he pr cipi is filtered,Washed with appropriately selected chlorinated organic acid in 3 8111811am un methyl alcohol. and then the continuous presence of ammoniumchloride. with some 9 methyl alcOhOl- Y treating the 3. A process forthe production of amino acetic alittle water, fil erin d adding alcohol.about acid in the continuous presence of ammonium I 10% more crudeaminoacetic acid is obtained. h o d W en dried, the to l amount o damino- 4. A process for the production oiv amino-pro- I acetic acidobtained amounts to about 4'. lbs. picnic a id which comprisesammonolysls or 4o h crude acid is dissolved in about literschlor-propionic acid, in the continuous presence 5 of water, underheating. Aiter treating the soluof ammonium chloride. tion with charcoaland filtering, about liters 0! methyl alcohol are added. After standingfor WILLIAM H. ENGEIS. several hours, the mixture is filtered, washedfirst GUSTAV A. STEIN.

